Preparing for Transaction

Diligence will expose every gap you haven’t fixed. I’ve done cyber diligence on 40+ acquisition targets and integrated 8 acquisitions. I know what buyers look for and what kills deals.

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Why Act Now

Diligence will expose every gap you haven’t fixed. The clock is already running.

You Might Be Experiencing This If…

  • You’re preparing for an exit, acquisition, or capital raise
  • You’re not sure what diligence will find when buyers look under the hood
  • Your security and compliance documentation is incomplete or outdated
  • You’ve been told your operational maturity will affect valuation
  • You’re acquiring a company and need to assess what you’re buying
  • Integration of a recent acquisition is exposing gaps you didn’t expect

What Success Looks Like

You control the narrative instead of reacting to it. Your security and technology posture holds up to buyer scrutiny. Diligence doesn’t expose operational debt that costs you on valuation. You’re positioned as transaction-ready, not transaction-risky.

How I’ve Helped Companies Like Yours

40+ Acquisition Targets

Done cyber diligence on 40+ acquisition targets across MSP, healthcare, manufacturing, and professional services. I know what buyers look for and what kills deals.

8 Integrations

Led post-acquisition integration 8 times. I know where the landmines are and how to avoid them.

$300K Savings

Identified $300K in annual IT cost savings during a single integration assessment through vendor consolidation.

“Rick was consistently vigilant in maintaining executive-level awareness around risk and frequently took the lead in navigating customer security incidents that required coordination across legal, IT, and regulatory teams. He is a trusted voice, a steady hand in critical moments.”

Jay Krupp, SVP Account Management Services, Miva, Inc. LinkedIn

Related Resources

Embedded Executive

Build transaction-ready security and technology. Embedded leadership through diligence and beyond.

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Executive Advisor

On-demand counsel for transaction preparation. Board and investor prep included.

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Frequently Asked Questions

Ideally 12-18 months before you expect to transact. That gives enough time to build real capability, not just documentation. If you’re 6 months out, we can still make meaningful progress, but you’ll be fixing gaps under time pressure. If diligence is already underway, we can help manage the process, but options are limited.

They’re assessing risk: Will this company create liability? Will integration be painful? Specifically, they look at security program maturity, incident history, compliance posture, technical debt, and key-person dependencies. I’ve been on both sides of 40+ deals. I know what gets flagged and what passes scrutiny.

Yes. I’ve done cyber diligence on 40+ acquisition targets. I can help you assess what you’re buying: hidden technical debt, integration complexity, security gaps, and realistic remediation costs. Better to know before you close than discover landmines after.

Post-acquisition integration is one of my core areas. I’ve integrated 8 acquisitions and know the common failure modes: systems that don’t talk, teams that clash, and complexity that compounds daily. The sooner you unify, the less painful it is. See the Integration situation page for more.

Operational and security maturity directly impact deal terms. Buyers discount for risk. If diligence exposes gaps, you’ll either lose value in negotiations or deal with escrow holdbacks and indemnification demands. Being transaction-ready means you’re not the deal risk.

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The Operator’s Take is complimentary. Let’s make sure diligence isn’t a surprise.

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